Ramble On
by skybound2
Summary: This may be the longest conversation that Sam and Dean have ever had that wasn't about a case. Sam wishes it wasn't about his brother's former...relationship...with Crowley, or that it hadn't taken Sam's questionable moral choices to get it started, but hey! There are worse ways to spend a nine hour car ride. Right? Or the one where Sam should really quit while he's ahead.


**Summary:** This may - just possibly - be the longest conversation that Sam and Dean have ever had that wasn't about a case. Sam kind of wishes it wasn't about his brother's... _relationship_...with Crowley, of all things, or that it hadn't taken Sam's questionable moral choices to get it started, but hey! There are worse ways to spend a nine hour car ride.

Right?

Also known as the one where Sam should really quit while he's ahead.

 **Author's Note:** This takes place during episode 12x15, _Somewhere Between Heaven and Hell_. Let's just pretend that the damage to the Impala following Sam's run in with Ramsey wasn't THAT bad, shall we? Title is borrowed from the **Led Zeppelin** song of the same name. Hope you enjoy!

* * *

 **Ramble On**

* * *

Sam loves his brother. He does. Honest. But right now? He kind of wants to throttle him.

"You're such a priss."

"Oh, Snookums, you say the sweetest things."

Crowley too. But that's standard operating procedure at this point.

"Stop being an uncooperative dick for three seconds-"

"Oh my dick is plenty cooperative. Care for a demonstration?"

 _Throttle. Them. Both._

His brother and the demon have been at it since Crowley announced he would join them on the hunt for Ramsey; informing them that they could narrow down the hound's location by making a quick jaunt to the kennels in hell and using her bedding for a locator spell.

(Sam couldn't make this shit up if he tried. This is just their life.)

That was _ten minutes ago_ , though it feels like years to Sam. Rather than vanishing off to do what he _said he was going to do,_ Crowley's...stuck around. For no reason Sam can see other than the joy of antagonizing Dean.

And Dean's _feeding_ it.

Hell, if he didn't know better, Sam would think that Dean almost looks like he's _enjoying_ it.

But that can't be right.

Sam sucks in a lungful of air, and tries once more to break the two apart, "Hey guys, can we-"

"I wasn't the one that started the name calling."

"Excuse me, _Boris?_ Half the words out of your mouth are insults."

"But I do it with _affection_."

And fails. Again. Sam sends an apologetic grimace towards Gwen; who seems more amused than annoyed.

He envies her.

"I don't see why _I_ have to go."

"It's _hell._ You're a _demon_. And oh yeah, _you run the freakin' place_. Who _else_ we gonna send?"

"Both Moose and you are familiar with-"

"Not happening."

"Now who's being a priss?"

"Says the King of Asshats."

Sam closes his eyes, breathes out through his nose, and promises himself that he will _not_ engage in fratricide.

He might murder a particular demon though, if they keep this up; and then where will they be?

 _We will be down one incredibly annoying, over-powered demon that can never seem to decide what side he's on._

 _Oh, and we'll still have a feral hellhound on the loose._

Sam sighs, the choice (for the moment) is clear.

He can strangle Crowley later, but for now, they need him.

 _Ugh_.

"Are you gonna whine all night, or are you gonna start being useful sometime before we're all dead?"

"I'm _here_ , aren't I? I told you what you're up against, and what you need to find her. Not my fault you refuse to step outside your comfort zone-"

"My comfort- You have a velvet padded _throne_. You wear bespoke _Armani_. You are one of the most self-pampered sonofabitches I have ever met, and you-"

Sam's brain glitches for a second on Dean's correct use of the word 'bespoke.' When it reboots, they're still going at it. He decides that air is what he needs. Air and distance. So he doesn't kill anyone. He turns to Gwen, "Where's your restroom?"

It takes Gwen several moments to tear her eyes away from the spectacle that is Dean and Crowley. Sam does his best to keep a patient smile on his face and to not look like he's three heartbeats from running away screaming. Or committing murder. "Uh...round the corner, down the hall to the left."

"Thanks."

Sam paces himself as he leaves the room, desperate to get away from the squabbling that's like needles in his brain, but also wanting to make sure he maximizes his time away.

Gwen's house isn't large, so he finds the bathroom with ease. After a quick splash of water against his face, he counts backwards from ten. Somewhat dazed by the verbal tennis match he'd just been witness to in the living room. He's not sure if Crowley's dragging this out in a deliberate avoidance of returning to hell like Dean seems to think, or if he's doing it as a punishment over what happened with Gavin.

Sam's money is on the latter.

Well, that, or he's just doing it to be an asshole.

Most likely a combination of the two.

Regardless, he wishes it would stop.

Sam stays in the bathroom, doing nothing more than hiding (and okay, checking his email), for longer than he knows is reasonable. For certain it's longer than any normal person would need to use the restroom, absent of some horrible intestinal problem. But the quiet is just so nice that he loathes the idea of leaving.

And hell, he doubts either Dean or Crowley have even noticed he's left.

In the end, he only opts to leave when he starts to worry that so much time has gone by without him there to intervene, that his brother may decide to throttle the demon for them both.

Which, he reminds himself, would be _bad_.

Steeling himself for his return, he takes a deep breath and opens the bathroom door. As it turns out, fate's decided to throw him a bone, and he catches the tail-end of Crowley's departure when the demon tosses out a disconcertingly cheerful " _Tootles_ " at the same moment.

Exhaling a sigh of relief at the short-term reprieve he's been given, Sam heads back towards the front room where his brother and their host wait. He's just rounding the corner of the hallway when Gwen's voice stops him in his tracks.

"Your Ex seems...nice."

Sam chokes on the air in his throat. Because that sentence? Makes _no sense._ _Nice?_ Was she _not_ listening to the same bicker-battle that Sam had been? How the _hell_ did she get _nice_ out of that? And also...

Did she just refer to _Crowley_ as Dean's _Ex_?

 _What? How?_

 ** _What?!_**

On the other side of the wall separating Sam from Dean and Gwen, Sam can hear Dean scoff. Wry amusement bleeding through in a half-laugh that isn't at all the copious sound of disgusted denial that Sam would expect at such a statement. "Don't let him hear you say that."

"Why not?"

"Crowley's a whole proud mess of contradictions. But 'nice'? Doesn't rank."

It takes Sam longer than he'd admit to parse out the multiple reveals in that statement.

At the top of which is the fact that Gwen called Crowley Dean's Ex, and Dean... _didn't correct her_.

The absence of the correction seems to seal Sam's feet to the floor. Sure, Sam had often mocked Dean for his 'Summer of Love' with Crowley, but he'd never actually thought...Ugly curiosity and something he'd rather not name holds him in place while his brother and Gwen's conversation trundles on in the next room, unaware of his proximity.

"Still though. He came as soon as you called. Offered to help. Despite seeming pretty angry when he answered the phone. Not too mention uncomfortable with even being here."

Dean grunts. "Yeah, well. It ain't about him being nice. Anything Crowley does, you can bet he has a half-dozen reasons for doing. If nothing else, he's reliable on that front."

Gwen makes a muffled sound that might be amusement, or maybe confusion; Sam's not sure. But, whatever it is, it prompts Dean to continue, much to Sam's bafflement.

"Trick is knowing how best to sell him on yours."

Sam can hear the smile in Gwen's voice, for all he can't see it through the wall. The exact opposite of the facial gesture that is pulling down the corners of his own mouth. "So you knew you could sell him, huh?"

"Knew? Nah. Crowley's a demon. Likes to be contrary just because he _can_. But, I knew the odds were in our favor. Hellhounds...they're kind of his thing."

"Well, in that case. I'm grateful you've managed to maintain enough of a civil relationship after your split that he's willing to help, for whatever reason."

"That sounded civil to you?"

"More civil than the aftermath of some of my break-ups, yeah." Gwen's voice trails off at the end. Her tone going soft, and maybe a little watery. And if Sam were in a state of mind to be thinking about anything _other_ than the fact that not only has Dean _still not corrected her_ he seems to be _going along with it as well,_ Sam would recognize this as a time when comfort is due, or at least some semblance of sympathy offered to the girl, and so he should pick his feet up and move into the room where they can see him, and say...something.

But he's not, and Dean _still hasn't corrected her. S_ o he can't, and he doesn't.

"It's been...better, lately." There's a weight to the words as Dean breathes them out that Sam can feel in his bones. It's shaped like Castiel; beaten and bloodied, dying on a dirty sofa; lit up like a starburst by the light of a broken staff.

"Hell, not like it could get much worse. When we…" Dean clears his throat. The sound dry, and maybe just a bit brittle. Sam's nerves feel the same. "Wasn't exactly the stuff dreams are made of."

"That bad, huh?"

And all Sam can think, is ' _Why is Dean_ telling _her_ any _of this?'_ laced with a liberal dose of _'How the fuck did I_ miss _this?'_

"I was a demon at the time. You think maintaining something healthy is hard when you're human? It's a damn cakewalk in comparison."

"You...were a demon?"

"Occupational hazard. I got over it."

"Oh. Huh. Okay. You guys have really weird lives."

"Believe me, we've noticed."

The conversation - thankfully - peters out. A minute later, Sam finds that the lead weights in his feet have lightened up enough for him to reenter the room. He schools his features best he can, and prepares to pretend there aren't explosions going off in his head from the information dump he just received.

Not that it matters. As soon as he's in the room, Dean stands, brushing his hands over his knees as he does, and asks Sam if he's ready to go. Looking for all the world like he wasn't just having a somewhat intimate discussion about his ( _what the fuck?!)_ romantic entanglement with the King of Hell, _with a complete stranger,_ or anything. When Sam doesn't hop to right away, Dean cocks an eyebrow and gives him an impatient frown.

So Sam does the only thing Sam can think of to do.

He shoves the memory of the whole, disturbing conversation far, far, _far_ into the back of his mind, and nods.

And for the next several hours he pretends he never heard a thing, doing his best to focus on the case.

He guesses he's about seventy-five percent successful.

He's not sure if it's better or worse when he's left with Gwen, and Dean goes off alone in the woods with Crowley.

No. Scratch that. He's sure. It's worse.

One hundred times worse.

Distracted, disturbed, and confused as all living fuck, Sam somehow manages to be more of an asset than a liability during the hunt (he's a professional dammit), and eventually the wayward hellhound has been dealt with.

That done, Crowley buzzes off back to hell or, _wherever,_ much to Sam's relief, and they see Gwen home on their own, Dean scowling at the condition of the Impala the whole time.

Sam about bites his tongue off keeping his mouth shut.

* * *

~~~\/~~~

* * *

Turns out, aside from the windshield (which is shot) most of the damage to the car is cosmetic.

Dean produces some kind of car emergency first aid kit from the depths of the trunk, and sets to work pulling up the dents in the hood so it doesn't impair the engine too much. He then pours some kind of magic resin on the windshield and tapes the glass before climbing in and starting the car; doing a fistpump in the air when the engine turns over without issue.

Sam frowns. While it does look a little better, it also doesn't look at all safe. "Is that gonna hold for the whole drive home?"

Dean shrugs. "It's held worse for longer. It'll be fine. Now get in, I'd like to make it home by sunup, less chance of getting pulled over that way."

"Fine. If you're sure."

"Trust me."

And Sam does, of course. Though he reserves the right to shout 'I told you so!' at the first sign of the windshield caving in.

Besides, Dean's right, it's not that long of a ride home. Nine and a half hours. Not an easy ride in one go, but they've had worse.

Nine and a half hours until they make it home, and Sam considers it a rousing success when he manages to hold back from spouting out all of his thoughts, questions, concerns and _what the absolute fucks_ for all of five miles. After which the dam breaks and the words come rushing out.

"She called Crowley your Ex."

Sam waits a beat for a response, expecting _something._ A laugh. A denial. A scoff. A nervous titter. A...a _blush_. _Something._ But...there's nothing. Dean doesn't so much as flinch. Doesn't even turn his head to look at Sam, doesn't do anything but keep on driving, fingers tapping against the wheel in time with Metallica pouring out of the speakers.

So Sam presses. _How can he not?_ "And you...didn't correct her."

"You asking a question, Sam, or just confessing to eavesdropping?"

Sam huffs a sigh, frustrated. "Come on, Dean."

"What, Sam?"

"You know what, Dean!"

"Do I?"

"Yes."

"You want an answer, Sam, ask a damn question."

"Fine. Were - Did you - was she - _is_ Crowley an _Ex_?"

Dean's face does this amazing thing where it contorts into a half-shrug nod using only his mouth and the back-and-forth motion of his chin. "For lack of a better term, sure. Let's go with that."

"What the hell does that mean?!"

"It means I was a demon at the time. Mostly. No real Facebook qualifier for that scenario."

Sam's brain catches on the 'mostly' part of that statement. The word flashing in bright neon letters at the front of his skull, until his head starts to pound. There was no 'mostly' when Dean was talking to Gwen, and Sam can almost, _almost_ wrap his mind around the idea of his brother and...and _Crowley_ when his brother was a demon, because well, _demon_. But ' _mostly_ ' implies something else. And Sam's not sure what the hell to do with that information.

The fact that Dean just offered it up _when he didn't even have to_ makes it even more confusing. He could have just let Sam think that it was...but he didn't.

 _What the hell?_

Sam's mind chews on the information, poking and prodding and trying it's best to digest it, but in the end all he is left with is an inedible nugget of knowledge that he has no idea how to deal with.

Meanwhile Dean just keeps on driving like he's unaware of the internal freakout Sam is having.

"So you and Crowley….?"

"Yeah."

"But you...I mean….you're... _not_...was it because-"

"Careful, Sam."

The air between them gets thicker, heavy with warning. Dean's hands flex at the wheel until the knuckles look white. The first sign of real emotion that he's shown since Sam opened his mouth.

It makes Sam's brain stutter before it kicks into overdrive. Because Sam, for all that he considers himself open-minded, never giving a second thought - or a first one even - to a person's orientation, finds his worldview tilted in a way he's not prepared for. He's always assumed that his brother was straight. There's never been a reason for him to question that.

Has there?

But clearly, there _must_ have been, and Sam just never noticed. Maybe he should have given a few more thoughts than the none that he did before coming to what was clearly a wrong conclusion.

And now that he's allowed the concept in, it's like he's torn a blindfold off, and his mind starts being helpful again. Offering up moment after moment, memory after memory of conversations he's overheard, of interactions that just ghosted past him. Moments of that low-level charm that Dean would ply guys with as easily as he would girls, that Sam always assumed was just Dean being manipulative and not… Or memories of Dean getting flustered when a guy would hit on him, and Sam had always figured that Dean was just embarrassed, not that he might be _…_ Or Dean guiding Charlie through how to _flirt_ with a _guy_ …

It all starts slotting together, in such a quick fashion, that Sam's embarrassed that it took him his whole life to solve a puzzle he didn't even realize he should be working on; but it took a person they just met all of one conversation to piece it together.

His mouth opens and shuts around a question he can't fully form, uncertain what it is he even wants to _ask_ , before he gives up, opting instead to just stare out the cracked windshield feeling like an inattentive bastard who doesn't know the first thing about his brother.

Dean sighs, a slow whiff of air that ends when he reaches one hand up to scratch at the back of his neck. "Go ahead and ask, Sammy."

And maybe Sam's imagining it, but now that he's paying attention to Dean, _really_ paying attention, all of the little tells that his brother is trying to hide become obvious.

And they all add up to one thing: Dean's _nervous_.

The realization brings Sam up short.

Because as much as he wants to understand the whole... _relationship_ … between Dean and Crowley (starting with how the _fuck_ that could be an accurate description in the first place) it's now gone to a much more serious place. Which isn't something Sam would have thought possible thirty minutes ago, but there you have it.

His brother is...

 _Gay? Bi? Pan?_

Not straight.

Sam shakes his head to clear his racing thoughts. Whatever the label, the fact is that his brother is...and Sam _never realized_.

"I'm an idiot."

"Not gonna argue with you there."

Sam huffs out a muted laugh, letting the bit of levity wash over him. "Thanks."

"You said it, not me."

"You're my brother. I should have…" Sam trails off. Because what the hell can he say other than 'he should have'?

Dean begins tapping out against the steering wheel in time with the music again, his knuckles no longer squeezed tight around it. "Maybe. But, it's not like I was going out of my way to advertise it to you."

"I-" There are a hundred questions Sam could ask. Most of which Dean probably expects, but what comes out instead is: "So why tell Gwen?"

"I didn't."

"She just...knew?"

"Nah. I mean, she might've, I don't know. But she also had some help from Crowley." At Sam's confused look, Dean (for once) seems to take pity on him and elaborates. "He's careful around you. 'Round Cas. Other demons. Knows it wouldn't end well if he wasn't. But he's never given a damn about being subtle with random people who he thinks don't count. Soon as you were out of the room, he said something that couldn't be taken as anything other than what it was."

Sam considers asking what the comment was, but then imagines what Crowley, the King of Innuendo, would consider _not subtle_ , and thinks better of it. "But you and Crowley. You're not. Together. Anymore. Right?"

"No. We're not."

"Okay."

"Okay?"

"Yeah. Okay."

It's what he says, and he even thinks he means it when the words first rush out. But when five minutes of unchanging midwestern scenery flow by without Dean offering up any additional information he can't stop his mouth from opening again.

"Since we cured you?"

Dean doesn't answer. Just gives Sam a look that tells him maybe he shouldn't push it. But Sam's self-preservation skills are obviously on the fritz, and so, push it he does. "Dean? It ended when we cured you."

"How honest you want me to be here, Sam?"

Sam thinks about that. Thinks about all the information he's received tonight and is desperately trying to unpack. But his brain is still tripping over and sticking on the 'mostly' that Dean used to describe the **when** of his and Crowley's... And God help him, but he's _curious._ "I'm not looking for details or anything-"

"You sure 'bout that? Cause I gotta say man, sounds like you're fishing."

"No! No. God, no. I just - I'm just trying to understand."

"Understand what?"

"How it...how it happened. I mean, it's _Crowley_."

"Yeah."

Sam flounders, his inability to get a read on his brother leaving him feeling wrong-footed. "He's a demon."

The look Dean gives Sam can only be categorized as dangerous. "Remind me, what was Ruby again?"

"We're not talking about Ruby. And even if we were, I've admitted - on multiple occasions - that was a huge mistake."

"Do you hear me saying that Crowley wasn't?"

No, he doesn't. But neither has Dean stated - explicitly - that he _was_. And that...that's _important_.

"Was he?"

"What do you think, Sam?"

"I don't know what to think, Dean! The way you were talking to Gwen it sounded…" Sam draws in a long breath, taking a moment to run both his hands through his hair, before digging his fingers into the corners of his eyes to press back at the throb that has become more pronounced the longer the conversation has gone on. "What happened with Ruby was a mistake. Okay? I trusted her when I shouldn't have. Obviously. Used her as an excuse to do things I knew I shouldn't. Just like she was using me to get what she wanted. It wasn't...it wasn't a _relationship_ , and I wouldn't call her an _Ex_."

"Well she's dead, so you've got help on that front."

"Come on, Dean."

"Whatd'ya want me to say here, Sam?"

Sam shrugs. Hell if he knows, but… "The truth might be good."

Dean sighs. Seconds tick on into minutes, and the tape in the deck comes to an end. Static from the radio fills the air for a few seconds as Dean flips it over and hits play again without saying a word, and Sam figures he's done talking.

One song bleeds into two, and Sam allows his focus to drift to the scenery passing by the dark windows, trying not to be disappointed that the conversation has ended. Not when Dean has been pretty damn open with him; something Sam knows is never easy for Dean, especially not with things that matter.

And this _matters_.

So Sam figures he can cut him some slack.

It's another twenty miles before either of them say anything again; and to Sam's surprise, it's not him.

"It started after I got the Mark. Alright? I was...The Mark fucked me up. In ways I can't describe, even if I wanted to. Which I don't. So don't ask. And Crowley - Crowley _got_ it. Made things easier. Didn't see any reason to change the status quo when I went dark."

Sam processes that as best he can. There's some sense there, he guesses. Though, how being with Crowley made things easier for Dean, Sam's not sure. And he's not sure he has it in him to ask just yet.

Still, while he might not be able to fully comprehend what having the Mark of Cain was like for Dean, or what being a demon did to him, he _has_ been hyped up on demon blood. And he's been soulless.

It's not the same, but he bets it's damn close.

And if the worse that had come out of Dean getting the Mark and becoming a demon had been his sleeping with Crowley? Well, they would have counted themselves lucky.

So yeah, if he tosses all his preconceived notions and ingrained biases in the dumpster where they belong, Dean turning to Crowley - it makes a kind of sense. And Sam can imagine that Crowley would have jumped at the chance to have that kind of sway with a Winchester, and an eventual Knight of Hell to boot. The bastard probably reveled in it. Except-

"Crowley led me to you. He's the reason I was able to find you so that Cas and I could cure you."

"I know. I was there, remember?"

"But if you and he-"

"We weren't anymore."

"Why?"

"I didn't want to dance to his tune. He wanted...a partner." Dean's fingers tap out off-time on the wheel, one hand reaching up to scrub at the crown of his head as he continues.

"He hates hell. Hates all the other idiot demons, and their incompetence. But he craves power. He wanted to, I don't know, restructure the whole thing, I guess. Wanted me to help make it happen. But I - I was a demon. And I'd spent my whole human life with responsibilities, and I was tired of it. I didn't want to be tied down to anything, or anyone. So I walked. Pretty sure he called you before the door had slammed shut behind me."

"Huh." Sam ponders that for a moment, one thought clicking faster than the rest, and he smiles at his brother, a laugh breaking through the heavy atmosphere without him even telling it to. "So... demon you was afraid of commitment? Good to know not everything changes when you get black eyes."

"Hardy har, Sammy." Dean says it with a straight face, but Sam can see the hint of a smile at the edge of his lips. He takes that as a good sign.

"The real funny part here is that Crowley is apparently less afraid of commitment then you are, demon or not."

Dean looks at Sam, one eyebrow raised. "You do realize that absent of someone like us coming around to ruin a demon's day, they can potentially live forever, right? No matter how much I liked hanging with the guy, I wasn't about to sign up for eternity with him."

Sam's still laughing when he says, "You liked him, huh?"

Dean shoots him a wry smile. "I was sleeping with him for a year. It's safe to say I liked at least _something_ about him."

"Oh, _ugh_ , Dean. I didn't need to hear that!"

"What you get for prying into my sex life."

"Fair point." Sam's laughter dies down as he thinks on the first, less uncomfortable part of Dean's statement. "A year?"

"Give or take."

Sam stares at his brother, unable to tear his eyes away. He watches as Dean squirms in his seat, just a little. If Sam wasn't so hyperfocused on him, he might have missed it. Or might have assumed it had to do with the length of time he's been driving.

But Sam is that focused, and so he doesn't miss it, and he's damn well done assuming anything tonight.

"You just said you ended things when you were still a demon."

"I did."

"That was less than a year after you got the Mark."

"It was."

"Dean?"

"Sam."

"Oh, _come on_." Sam throws his hands over his head, smacking at the roof of the car. He'd full well stomp his feet if he had enough room, no matter how childish the action would appear. "You can't just...just _say_ things like that, and not expect me to-"

"I ended it. Never said it _stuck_."

"Oh." Sam mulls that over for a minute. "But it's over now."

"It is."

Sam's next question is obvious to them both, but he knows he has to ask or Dean won't answer. "When?"

"Don't know. Wasn't like I was keeping track. Sometime before Amara."

"Why?"

"Why what?"

"All of it?"

Dean rubs a hand across his lower jaw, slanting his eyes towards Sam. "For someone who claimed he didn't want details, you sure are digging here."

Sam knows Dean's right. He is digging. More than he should. But Dean's also _answering_ , albeit grudgingly. So he's not quite willing to put the matter to rest.

"It's...if it was _just_...sex." The word sticks in Sam's throat, but _dammit_ , he's an adult. He can have a conversation with his brother about...sex with Crowley?

Yeah, no. He needs to not think about it in those terms, because that way lies madness.

"If it was just sex, you wouldn't have said it was 'complicated' or -" Sam blinks, realization flaring bright in his brain. "Oh my god. That argument at Gwen's house. You were like a divorced couple forced to spend time together."

Dean shifts in his seat again. "I wouldn't go _that_ far."

"How far _would_ you go - and that is _not_ meant to be a double entendre."

Dean doesn't even look like he's tempted to take the bait, however. Which on a normal day would be cause for concern, but in this case, Sam's just grateful.

Instead, Dean remains silent as he switches lanes; fingers tapping off-beat on the steering wheel while Steppenwolf switches to Hendrix.

A dozen mile markers pass by before he answers; surprising Sam yet again by his willingness to keep the conversation going without direct prompting.

"It's not like it was some epic lovefest. Hell, half the time I couldn't stand him."

Sam knows he shouldn't ask. He shouldn't. But also, how can he _not_?

"And the other half?"

"Sex was good." Dean says it with a shrug, just focusing on the road with a small frown on his face that doesn't quite match the one on Sam's.

"We played foosball. Got drunk. Watched TV. Picked up chicks together. It wasn't...If Crowley wasn't just angling to get me to drink the demon kool-aid and go all in evil with him, and if I'd had an ounce of ability to give a shit about anything at the time, I would have called us friends." Dean's one hand drops to his knee, scratching over the denim; the other remains tapping away on the wheel.

"After the cure- I still had the Mark, and...being with Crowley was...easier. Safer. Then being with anyone else."

"Safer?"

Dean swallows. "The Mark. It- I didn't have to worry about...hurting him. Not like I would someone...human." Dean appears uncomfortable at the confession, and Sam can relate. He's uncomfortable hearing it, though he suspects it's for different reasons.

"But then he'd go and pull his usual shit, hell, sometimes he was even _worse_." Dean shakes his head. "Helped me remember what the hell he was. What I didn't want to be. Why it needed to stop."

Sam recalls the way that Crowley broke during the cure that wasn't. Recalls the way that his head hung low, and how his whole frame hunched over itself as he asked Sam how he could find forgiveness. _'Where do I start?'_

Recalls how since then, Crowley's always been a hair quicker to lend a hand, and a hair quicker to turn on them when they least expect it.

Recalls Crowley calling Dean his _bestie,_ and wonders how much of what went down between his brother and the demon was Crowley playing a long con, and how much of it may have been the result of honest - if twisted - affection he was feeling.

The fact that Sam can't quite rule out the second option is hard to process.

Hell, after the whole human blood addiction debacle, it even seems plausible.

Which may mean he started upping the bastard factor as a deliberate reminder to himself what he really was, and what he wasn't, as much as anything else.

That idea has merit, and it's unsettling how much that puts Crowley's behavior that year in perspective for Sam.

Equally unsettling is the fact that Sam is actually _trying_ to see things from Crowley's perspective.

And because Sam can't keep any of this thoughts to himself tonight, he asks "You think maybe he was behaving that way on purpose?"

Dean takes long enough to answer that Sam knows he's giving the question genuine consideration. "Maybe. Doesn't matter."

But Sam thinks it _does_ matter. He doesn't say anything along those lines though. Just settles into the silence that follows the lengthy discussion. His curiosity...abated, if not wholly satisfied.

Off to the right of the highway, a gas station shines like a beacon in the night. Dean flicks the blinker on, guides the car off the road, and pulls up to a pump. "Fill her up? I'm gonna hit the head."

The car door slams in Dean's wake, and Sam climbs out to do as requested, accepting the dismissal for what it is.

And that's fine.

He's got plenty to chew on as is.

* * *

~~~\/~~~

* * *

Sam plans to lay off his brother for the rest of the trip, he really does. They spend the next couple of hours in silence, mixtapes filling up the void between them.

Sam had hoped that the time would allow him to organize all he's learned, and that he'd be able to put the matter to rest.

He should really know himself better by now.

In reality, it just allows him time to organize the multitude of questions he has. And one after another, they force their way out of his lungs and into the open; where he can never take them back.

"What the hell is this, Sam? Did I miss the memo where we both agreed to be teenage girls for the night?"

"That's not fair, Dean. You're my brother, and there's this huge part of your life I had no idea was even a thing. Can you blame me for wanting to know-"

And here Sam can admit, he could have _possibly_ been more artful with how he expressed his curiosity.

During the downtime, Sam had thought about how he never knew about Cassie or Lisa until it become relevant to their job. And he wondered, in all innocence, if there had been anyone else that Dean had been close to that he'd never told Sam about. Someone, perhaps, a damn sight _less_ demonic than Crowley.

Someone his brother may have had a _healthy_ relationship with, for any length of time. Even if it was long since over.

Sam was really hoping that he _had._ But for some reason, that sincere hope results in a question so lacking in tact that Dean's response, through the thin press of his mouth, is: "You wanna know if it was Crowley that popped my cherry, that it? The answer's no. So no need to get your painties in a twist about it."

"What?! No. What?" Sam goggles at him. "That is **not** what I was getting at and you know it."

"Could've fooled me."

Sam digs his fingers into his thighs, annoyed with himself for being careless and annoyed with Dean for being so obtuse. "I was trying to ask if there'd been anyone-"

"What you want a list?"

Sam chokes. No. No he does not. _But_. Curiosity, thy name is Sam. _"There's a list?"_

Dean rolls his eyes, the action obvious in the lights of oncoming traffic. "Not really. But the number ain't small. Most of 'em gone just as quick as you'd expect."

And now they're getting to the heart of what Sam has been _trying_ to ask his brother, in what has been - admittedly - a very inept manner. "Most of them?"

Dean does that odd half-shrug thing with his face again. "There were a couple that stuck around longer than a weekend."

"Other than Crowley?"

"Yeah, Sam. Other than him."

Sam lets the comment linger for a few moments, making sure his next question can't be taken in any way other than how he intends it. "Longer than a weekend, like, made it a whole week, or longer than a weekend like...Lisa...longer than a weekend?"

Dean doesn't answer, just pinches the bridge of his nose; scraping the hand down over his face and dropping it back onto the steering wheel.

Sam's use to the lingering pauses in the conversation by this point, so he waits it out with just an occasional glance at his brother from the corner of his eye. He's relieved to see that Dean now looks more pensive than he does pissed.

A swipe of his phone screen tells Sam they still have another six hours of driving ahead of them.

He waits.

 _Five hours and forty-five minutes._

"Two. There were two. Alright?"

Sam mulls this over, trying to figure out how to cull his mountain of questions down to a short, inoffensive stack that Dean might be willing to answer. What he settles on is less than inspiring, but it's the middle of the night, and Shakespeare he is not. "What uh, what happened?"

Dean's fingers tap along to the song coming low through the speakers until Ozzy's vocals have given way to Plant's.

"One of them was just timing. Was right after you went off to college. I was hunting pretty regular. Moving around a lot. But I'd been in one place long enough that I'd seen someone more than a few times. Moved again soon enough and it just sorta...faded out. No muss no fuss. It was good for a while though."

There's a faraway look on Dean's face that Sam can tell in profile is a little bit wistful, and a little bit fond; like Dean's stuck in a happy memory. So of course Sam has to ruin it.

"And the other?"

Dean's jaw clenches as he looks up at the roof of the car before swinging his eyes back to the road, and then turning to Sam, holding him with a steady gaze for a few beats longer than is safe, given the fact that he's still driving. "I cut his head off so you'd have a way out of Purgatory."

Sam's brain crashes to a halt. He blinks dumbly at his brother. Because of course, _of course,_ Dean and Benny were _..._ "Oh."

"Yeah. We done?"

Sam's heart thumps over in his chest, and he nods. Grateful when a few road markers later, Dean reaches out and turns up the volume. The conversation drowned out by the Stones.

* * *

~~~\/~~~

* * *

 _Four hours and thirty-one minutes._

"...You knew I was listening, didn't you? Back at Gwen's house."

"You're a walking redwood tree, Sam. Subterfuge isn't your strong suit."

"Hey! I can be subtle."

"No. You really can't."

"Thanks a lot."

"Anytime."

Sam chews on his lip. "Why didn't you say anything?"

"Figured you'd have that covered plenty at some point. And look! I was right."

"Jerk."

"Bitch."

* * *

~~~\/~~~

* * *

 _Three hours and fifty-six minutes._

"I'm sorry. About Benny."

"The fuck?" Dean's head whips around towards Sam, his eyebrows at hairline level and the car swerving with the abrupt motion. Thank God there's zero traffic at this hour.

Sam waits for Dean to get the car back between the lines, his heart pounding at his ribcage, before he says anything else. His brother's involuntary response almost more telling than anything that's been said the whole night.

"For what happened. I wasn't...I was the actual opposite of supportive there. I know. You told me what he'd done for you in Purgatory, and I should have...respected that. And you...you-" _Loved_ "Cared about him, didn't you?"

Dean doesn't look at Sam, but he swallows, and takes a long-drawn out moment to respond. His voice rough around the edges when he says, "Yeah. I did."

Sam nods. An awful, heavy sensation in his gut telling him that he should have done _something_ to get Benny to leave Purgatory with him. Anything besides tossing him a blade and being secretly grateful that he didn't have to cart the vampire out of the place inside his own body.

"I'm sorry."

Dean shrugs, a half-hearted, barely there sort of a gesture that looks like it hurts. "Nothing for you to be sorry about. He made his choice. Not the one I wanted him to make, but…" The thought sits there, unfinished. Sam thinks of all the could've would've should've beens he's had in his life too, and thinks that's all that needs to be said on the topic.

For now at least.

* * *

~~~\/~~~

* * *

 _Three hours and three minutes._

"Did you tell Gwen everything you did _because_ you knew I was listening?"

Dean gives Sam a distracted "Hmm?" in response, which Sam takes to mean _'Sorry, Dean's brain isn't paying attention to you right now, please try again later.'_

Sam gives it one mile marker, then dutifully tries again. The response he gets this time is a distinct improvement.

"We're getting old, Sam. It's exhausting keeping shit from you when it really doesn't need to be."

"I get that. There may have been an easier way of going about it though."

"Like what? A hallmark greeting card?"

"...You could have just _told_ me."

"I'm sorry, have we met?"

* * *

~~~\/~~~

* * *

 _Two hours and forty-seven minutes._

"Hey, Dean-"

"Sam, I swear, if the next words out of your mouth have anything to do with my romantic or sexual history, _in any way_ , I'm gonna launch into obscene and graphic detail about the time Crowley and I tag-teamed a set of triplets. I'm talking Best of Redtube detail, none of that Penthouse Forum nonsense."

"That's not-"

"Male triplets, Sam. Smokin' hot ones."

Sam doesn't pout. He _doesn't_. He's a grown man.

He may slump in his seat though. Just a tad. The angle makes it hard to speak, so that what he says next comes out in a mumble. "I was just gonna ask if we could take the next exit. Water's all gone, and the only snacks we have left are that bag of pork rinds that have been in the glove compartment since I went to college."

"We have pork rinds? Gimme." His brother's hand reaches out in a grasping gesture, and Sam hands the bag over, watching in amazement as his brother tears into it with gusto.

"Ew, Dean."

"What?" Dean says around a mouth full of questionable snacks. "They're delicious."

Sam tries not to gag.

* * *

~~~\/~~~

* * *

 _One hour and thirty-nine minutes._

Sam's mind isn't his own anymore. Exhaustion having overtaken it hours ago, and shutting down his brain to mouth filter in an effort to conserve energy. It's the only reason why, completely without his say so, his brain - which has been unhappily _thinking_ about the logistics of...of... _that_ \- forces his mouth open to quietly express his confusion over " _Triplets?_ "

"I warned you, Sam."

Sam shoots up in his seat, adrenaline spiking in his veins like there's a Wendigo at his heels. "No! Dean, I didn't mean-"

Dean's eyes shine with sadistic glee. "Too late."

"Don't! Wait! Please?!"

* * *

~~~\/~~~

* * *

 _Fifty-seven minutes._

"..."

"..."

"..."

"Good talk."

"I hate you."

* * *

~~~\/~~~

* * *

The sun's coming up when they reach the bunker.

Sam stares wide-eyed at the orange-pink light reflecting like a kaleidoscope off the cracked windshield that, by some miracle, managed to stay intact for the whole drive.

He continues to stare as the garage door comes down, blocking out the light.

"Look at that. Record time."

At last, Sam blinks. "I'm never going to be able to look him in the eye again."

Dean laughs, the sound lighter and more carefree than Sam thinks it has any right to be, given what he's just done to him. "Oh, he'll love that."

"It's not funny, Dean!"

"Beg to differ." Dean puts the car in park, but stays seated, his body half-turned towards Sam. "You know you can't let on that you know, right?"

Sam's forehead crinkles. "What? Why?"

"Remember the part about him going easy around you? He catches on that you know? All bets are off. You think you're traumatized from what I just told you? Trust me, you don't want to hear what he'd come up with to make you blush."

Sam sputters. "He couldn't- there can't _possibly_ be anything worse than…" Sam trails off at the look Dean gives him; his eyebrows wiggling in a 'try me' gesture a little too reminiscent of the demon for Sam's comfort.

"Crowley was right about one thing, Sam. It can always get weirder."

Dean climbs out of the car, grabbing his bag from the backseat as he does. He slaps a hand down on the doorframe in parting as he heads inside. It makes the cracked windshield shake, a smattering of glass chips floating down to land in Sam's lap.

He doesn't leave the safety of the car for a very, _very_ long time.

~End

* * *

 **End Note:** I began this story immediately after 12x15 aired. Then the end of season 12 happened and I put this on ice. (I was in mourning, okay?) I picked it up again a few weeks ago when I decided that a companion piece that also serves as a 12x23 follow up fix-it fic was in order. That one is titled "Searching for Smoke" and will be posted as its own separate story shortly.


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